Clifford Glimmer (Paul Menezes) goes into advertising after college, but he got his name -- plus a lot of other blessings and problems -- from jazz. He was born to the trumpet-playing Gene (Chris Hoffman), who idolizes jazzman Clifford Brown, and whose main loyalties are to a coterie of quirky, loose, monomaniacal horn players who gig as side men in New York City. Nine-to-five jobs are anathema to these guys, and their lives are drug-addled, romantically labyrinthine, and financed by unemployment checks. It's Clifford who's to be the anchor of the Glimmer family in Warren Leight's jazz-steeped memory play, Side Man, directed with wit and sensitivity by Sara Stelk for the Freeport Players. In scenes that slip between the '50s and the '80s, this sometimes excruciating drama explores a sublime but fading calling, as well as all it can shunt to the margins.

The play's first zings come in the often-hilarious rapport and physical idiosyncrasies of Gene's horn-playing foursome: The lanky, hollow-cheeked, Jonesy (Barry Ribbons), looks like what you'd get if you crossed Abraham Lincoln with a hopped-up early Disney cartoon. Al (David Barham) is a swaggering, bearded Lothario with a libidinous laugh; and Ziggy (Hugh Barton) has a lumbering gait and a speech impediment. Gene, Clifford's dad, goes along in perpetual glide, as smooth and blithe as a Buddha with a spliff. These actors inhabit their characters with impressive depth as they drink, smoke up, talk shop, trade romantic turns with the saucy waitress/horn-groupie Patsy (Andrea Myles-Hunkin) and, most importantly, play. Then along comes Terry (the formidable Julia Langham), a tough but naïve divorcee from East Boston. From the moment she falls for Gene's gorgeous tone, it's clear that neither she, nor, later, their son, will ever compete with the camaraderie and passion the side men share.

Like some of the horn players, the Freeport Players have no permanent home. They're staging this show upstairs at 140 Main Street in a vast empty floor of an office building, where the whiff of modest squalor in a drop ceiling and fluorescent lights is actually somewhat simpatico with the hardscrabble characters. There's no lack of space here for David and Dorothy Glendinning's set, including the Glimmers' apartment and the Melody Lounge nightclub. In fact, I would cramp them a little closer together, for even more suggestion of both the cadre's intimate, hand-to-mouth living, and the often-overlapping settings of memory.

As Clifford slips forth and back in time, the cast ages and evolves with remarkable fidelity to the characters they draw. The arc of Langham's Terry is especially deft as continued hardship and disappointment change her hard-ass edge from plucky to violent and almost unbearably caustic. As for Clifford himself, it's not until we learn just how bad his childhood home life was that the depth of Menezes's nuance becomes clear. As a 10-year-old, eyes wide, he is as sensitive as a reed to his parents' moods and needs, rarely revealing a hint of his own.

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